Prof. Sawamura / Papers

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Prof. Masaya Sawamura (Original papers/Reviews/ Environment and Safety)

Original papers
Photoinduced Platinum-catalyzed Reductive Allylation of α-Diketones with Allylic Carbonates.
Shimosato, J.Sawamura, M.; Masuda, Y.  
Org. Lett., 2024, ASAP.
DOI: 10.1021/acs.orglett.4c00091  

Photocatalytic Aldehyde C–H Bond Phosphonioethylation with Vinylphosphonium Bromide.
Mori, H.; Yoshida, M.; Sawamura, M.; Masuda, Y. 
Asian J. Org. Chem., 2024, 13, e202300532.

Photocatalytic 1,2-Phosphorus-Migrative [3+2] Cycloaddition of
Tri(t-butyl)phosphine with Terminal Alkynes.

Masuda, Y.; Ikeshita, D.; Higashida, K.; Yoshida, M.; Ishida, N.; Murakami, M.; 
Sawamura, M.
J. Am. Chem. Soc., 2023, 145, 19060–19066.

Gold-Zinc Cooperative Catalysis for Seven-exo-dig Hydrocarboxylation of 
Internal Alkynes.
Sato, M.; Rawat, V. K.; Higashida, K.; Sawamura, M.  
Chem. Eur. J., 2023, 29, e202301917.
DOI: 10.1002/chem.202301917

Sheltering Mono-P-Ligated Metal Complexes in Porous Polystyrene Monolith: Effect of Aryl Pendant Stabilizers on Catalytic Durability.
Matsumoto, H.; Hoshino, Y.; Iwai, T.; Sawamura, M.; Miura, Y.
Chem. Eur. J., 2023, 29, e202301847.  

Dimetal-Binding Scaffold 2-(Pyridin-2-yl)imidazo[1,5-b]pyridazine-7-ylidene: Synthesis of Trinuclear Heterobimetallic Complexes Involving Gold–Metal Interactions.

Kitabayashi, A.; Ono, Y.; Taketsugu, T.; Sawamura, M.; Higashida, K
Chem. Eur. J., 2023, 29, Early View, e202301673 (Hot Paper).

Sequence-selective Three-component Reactions of Alkyltrifluoroborates with α,β-Unsaturated Carbonyl Compounds and Vinylphosphonium Salts.

Yoshida, M.; Sawamura, M.; Masuda, Y. 
Org. Chem. Front., 2023, 10, 3654-3661.
DOI: 10.1039/D3QO00631J

Visible-Light-Induced Aminochlorination of Alkenes.
Mejri, E.; Higashida, K.; Kondo,Y.; Nawachi, A.; Morimoto, H.; Ohshima, T.; 
Sawamura, M.; Shimizu
Org. Lett., 2023, 25, in press.
DOI: 10.1021/acs.orglett.3c01645

Direct α-Trifluoromethylthiolation of Carboxylic Acids Enabled by Boron Catalysis.
Sun, K.; Huang, C.-Y.(Dennis) ; Sawamura, M.; Shimizu, Y. 
Synlett, 2023, 34, 2210–2214.

Nickel-Catalyzed Defluorophosphonylation of Aryl Fluorides.
You, Z.; Masuda, Y.; Iwai, T.; Higashida, K.;  Sawamura, M. 
J. Org. Chem., 2022, 87, 14731-14737.
DOI: 10.1021/acs.joc.2c02048



Photoinduced Alcoholic α-C–H Bond Anti-Markovnikov Addition to Vinylphosphonium Bromides Followed by Wittig Olefination: Two-step Protocol for α-C–H Allylic Alkylation of Alcohols.
Yoshida, M.; Sawamura, M.; Masuda, Y. 
ChemCatChem., 2022, 14, e202200744(VIP). 
DOI: 10.1002/cctc.202200744



Construction of Heterobimetallic Catalytic Scaffold with a Carbene-Bipyridine Ligand: Gold-Zinc Two-Metal Catalysis for Intermolecular Addition of O-Nucleophiles to Non-activated Alkynes.
Rawat, V. K.; Higashida, K.; Sawamura, M.
ACS Catal., 2022, 12, 8325-8330.
DOI: 10.1021/acscatal.2c01701

Silver-Catalyzed Asymmetric Aldol Reaction of Isocyanoacetic Acid
Derivatives Enabled by Cooperative Participation of Classical and
Nonclassical Hydrogen Bonds.

Sakai, S.; Fujioka, A.; Imai, K.; Uchiyama, K.; Shimizu, Y.; 
Higashida, K.; Sawamura, M.

Adv. Synth. Catal.2022, 364, 2333-2339.
DOI: 10.1002/adsc.202200327

Insights into the Mechanism of Enantioselective Copper-Catalyzed Ring-Opening Allylic Alkylation of Cyclopropanols.
Kitabayashi, A.; Mizushima, S.; Higashida, K.; 
Yasuda, Y.;  Shimizu, Y.;  Sawamura, M.
Adv. Synth. Catal.2022, 364,1855-1862.
DOI: 10.1002/adsc.202200157

Visible Light-Induced Reductive Allylation of Aldehydes by Umpolung Approach.
Tanaka, I.Sawamura, M.; Shimizu, Y.
Org. Lett.2022, 24, 520–524.
DOI: 10.1021/acs.orglett.1c03927

Photoinduced Copper-Catalyzed Asymmetric Acylation of Allylic Phosphates with Acylsilanes.
Ueda, Y.; Masuda, Y.; Iwai, T.; Imaeda, K.; Takeuchi, H.; Ueno, K.; Gao, M.; Hasegawa, J.; Sawamura, M.
J. Am. Chem. Soc., 2022, 144, 2218–2224.
DOI: 10.1021/jacs.1c11526

Synthesis of C,N,N-Cyclometalated Gold(III) Complexes with Anionic Amide Ligands
Niizeki, R.; Higashida, K.; Mejri, E.; Sawamura, M.; Shimizu, Y.
Synlett, 2022,33, 288-292.
DOI: 10.1055/a-1673-9236


Visible-Light-Driven α-Allylation of Carboxylic Acids
Sun, K.; Ueno, M.; Imaeda, K.; Ueno, K.; Sawamura, M.; Shimizu, Y.
ACS Catal., 2021,11, 9722-9728.
DOI: 10.1021/acscatal.1c02558


Access to Indole-Fused Benzannulated Medium-Sized Rings through Gold(I)-Catalyzed Cascade Cyclization of Azido-Alkynes
Greiner, L. C.; Inuki, S.;  Arichi, N.; Oishi, S.; Rikito, S.; Iwai, T.; Sawamura, M.; Hashmi, A. S. K.; Ohno, H.
Chem. Eur. J., 2021, 27, 12992-12997.
DOI:  10.1002/chem.202101824


Nickel-catalyzed Homo-coupling of Aryl Ethers with Magnesium Anthracene Reductant
Rawat, V. K.; Higashida, K.;  Sawamura, M.
Synthesis, 2021, 53, 3397-3403. 
DOI: 10.1055/a-1509-5954


A Hollow-Shaped Caged Triarylphosphine: Synthesis, Characterization and Applications to Gold(I)-Catalyzed 1,8-Enyne Cycloisomerization
Iwai,T.; Goto,Y.; You, Z.; Sawamura, M.
Chem. Lett., 2021, 50, 1236-1239.


Use of Imidazo[1,5-a]pyridin-3-ylidene as a Platform for Metal-Imidazole Cooperative Catalysis: Silver-Catalyzed Cyclization of Alkyne-Tethered Carboxylic Acids
Rawat, V. K.; Higashida, K.;  Sawamura, M.
Adv. Synth. Cat., 2021, 363, 1631–1637.
DOI: 10.1002/adsc.202001515

Phosphinylation of Non-activated Aryl Fluorides through Nucleophilic Aromatic Substitution at the Boundary of Concerted and Stepwise Mechanisms
You, Z.; Higashida, K.; Iwai,T.; Sawamura, M.
Angew. Chem. Int. Ed., 2021, 90, 5778–5782.
DOI: 10.1002/anie.202013544

Synthesis of 2-Hydroxy-2-pyridinone Derivatives and Evaluation of Their Antioxidant/Anticancer Activities
Hamama, W. S.;  Ghaith, E. A.; Ibrahim, M. E.; Sawamura, M.; Zoorob, H. H.
ChemistrySelect, 2021, 6, 1430–1439.


Dumbbell-Shaped 2,2’-Bipyridines: Controlled Metal Monochelation and Application to Ni-Catalyzed Cross-Couplings
Kim, Y.; Iwai T.; Fujii,S.; Ueno, K.; Sawamura, M.
Chem. Eur. J., 2021, 27, 2289–2293.
DOI: 10.1002/chem.202004053


Convenient Synthesis of Binary and Fused Pyrazole Ring Systems: Accredited by Molecular Modeling and Biological Evaluation
Ghaith, E. A.; Zoorob, H. H.; Ibrahim, M. E.; Sawamura, M.; Hamama, W. S.
ChemistrySelect. 2020, 5, 14917–14923.


Polystyrene-Cross-Linking Triphenylphosphine on Porous Monolith: Enhanced Catalytic Activity for Aryl Chloride Cross-Coupling in Biphasic Flow
Matsumoto, H.; Hoshino, Y.; Iwai, T.; Sawamura, M.; Miura, Y.
Ind. Eng. Chem. Res. 2020, 59, 15179–15187.
DOI: 10.1021/acs.iecr.0c02404

Iridium-Catalyzed Enantioselective Transfer Hydrogenation of Ketones Controlled by Alcohol Hydrogen-Bonding and sp3-C–H Noncovalent Interactions
Murayama, H.; Heike, Y.; Higashida, K.; Shimizu, Y.; Yodsin, N.; Wongnongwa, Y.; Jungsuttiwong, S.;  Mori, S.; Sawamura, M.
Adv. Synth. Catal. 2020, 362, 4655–4661.
DOI: 10.1002/adsc.202000615 

Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine
Zhang, D.; Iwai, T.; Sawamura, M.
Org. Lett. 2020, 22, 5240–5245.
DOI: 10.1021/acs.orglett.0c01905

Polystyrene‐Supported PPh3 in Macroporous Monolith: Effect of Cross‐Linking Degree on Coordination Mode and Catalytic Activity in Pd‐Catalyzed C‐C Cross‐Coupling of Aryl Chlorides
Matsumoto, H.; Hoshino, Y.; Iwai, T.; Sawamura, M.; Miura, Y.
ChemCatChem 2020, 12, 4034–4037.
DOI: 10.1002/cctc.202000651

Copper-Catalyzed Enantioselective Conjugate Reduction of α,β-Unsaturated Esters with Phenol-Carbene Chiral Ligand
Mimura, S.; Mizushima, S.; Shimizu, Y.; Sawamura, M.
Beilstein J. Org. Chem. 2020, 16, 537–543.
DOI: 10.3762/bjoc.16.50 

Boron-Catalyzed α-Amination of Carboxylic Acids
Morisawa, T.; Sawamura, M.; Shimizu, Y.
Org. Lett. 2019, 21, 7466–7469.
DOI: 10.1021/acs.orglett.9b02769

Iridium-Catalyzed Alkene-Selective Transfer Hydrogenation with 1,4-Dioxane as Hydrogen Donor
Zhang, D.; Iwai, T.; Sawamura, M.
Org. Lett. 2019, 21, 5867–5872
DOI: 10.1021/acs.orglett.9b01989

Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines.
Nishizawa, A.; Takahira, T.; Yasui, K.; Fujimoto, H.; Iwai, T.; Sawamura, M.; Chatani, N.; Tobisu, M.
J. Am. Chem. Soc. 2019, 141, 7261–7265.
DOI: 10.1021/jacs.9b02751


Nickel-Copper-Catalyzed Hydroacylation of Vinylarenes with Acyl Fluorides and Hydrosilanes
Ueda, Y.; Iwai, T.; Sawamura, M
Chem. Eur. J. 2019, 25, 9410–9414.
DOI: 10.1002/chem.201900822.

Heterogeneous Nickel-Catalyzed Cross-Coupling between Aryl Chlorides and Alkyllithiums Using a Polystyrene-Cross-Linking Bisphosphine Ligand
Yamazaki, Y.; Arima, N.; Iwai, T.; Sawamura, M.
Adv. Synth. Catal. 2019, 361, 2250–2254.
DOI: 10.1002/adsc.201801713

Asymmetric Synthesis of α-Alkylidene-β-Lactams through Copper Catalysis with a Prolinol-Phosphine Chiral Ligand
Imai, K.; Takayama, Y.; Murayama, H.; Ohmiya, H.; Shimizu Y.,; Sawamura, M.
Org. Lett. 2019, 21, 1717–1721.

A Polystyrene-Cross-Linking Tricyclohexylphosphine: Synthesis, Characterization and Applications to Pd-Catalyzed Cross-Coupling Reactions of Aryl Chlorides
Arashima, J.; Iwai, T.; Sawamura, M.
Chem. Asian J. 2019, 14, 411–415.
DOI: 10.1002/asia.201801651

P,P,P’,P’-Tetraethynylated Bisphosphine and P-C-P Pincer Ligands with Bulky End Caps: Synthesis, Coordination Properties and Application to Platinum-Catalyzed 1,8-Enyne Cycloisomerization
Iwai, T.; Shibaike, M.; Sawamura, M.
Chem. Lett. 2018, 47, 1162–1164.
DOI: 10.1246/cl.180501

Palladium-Catalyzed Asymmetric C(sp3)-H Allylation of 2-Alkylpyridines
Murakami, R.; Sano, K.; Iwai, T.; Taniguchi, T.; Monde, K.; Sawamura, M.
Angew. Chem. Int. Ed. 2018, 57, 9465–9469.
DOI: 10.1002/anie.201802821

Synthesis, Properties, and Catalytic Application of a Triptycene-Type Borate-Phosphine Ligand
Konishi, S.; Iwai, T.; Sawamura, M.
Organometallics 2018, 37, 1876–1883.
DOI: 10.1021/acs.organomet.8b00113
Phosphine-Catalyzed Anti-Hydroboration of Internal Alkynes
Nagao, K.; Yamazaki, A.; Ohmiya, H.; Sawamura, M.
Org. Lett. 2018, 20, 1861–1865.
DOI: 10.1021/acs.orglett.8b00390
Enantiocontrol by Assembled Attractive Interactions in Copper-catalyzed Asymmetric Direct Alkynylation of  a-Ketoesters with Terminal Alkynes: OH···O/sp3-CH···O Two-point Hydrogen-bonding Combined with Dispersive Attractions
Schwarzer, M. C.; Fujioka, A.; Ishii, T.; Ohmiya, H.; Mori, S.; Sawamura, M.
Chem. Sci. 2018, 9, 3484–3493.
DOI: 10.1039/C8SC00527C
Copper-Catalyzed Enantioselective Intramolecular Alkylboron Allylic Alkylation
Hojoh, K.; Shido, Y.; Ohmiya, H.; Sawamura, M.
Chem. Lett. 2018, 47, 632–635.
DOI: 10.1246/cl.180147

Copper-Catalyzed Enantioselective Coupling between Allylboronates and Phosphates with a Phenol-Carbene Chiral Ligand: Asymmetric Synthesis of Chiral Branched 1,5-Dienes
Yasuda, Y.; Ohmiya, H.; Sawamura, M.
Synthesis 2018, 50, 2235–2246.
DOI: 10.1055/s-0036-1591548

Phosphine-Catalyzed Anti-Carboboration of Alkynoates with 9-BBN-Based 1,1-Diborylalkanes: Synthesis and Use of Multi-Substituted g-Borylallylboranes
Yamazaki, A.; Nagao, K.; Iwai, T.; Ohmiya, H.; Sawamura, M.
Angew. Chem. Int. Ed. 2018, 57, 3196–3199.
DOI: 10.1002/anie.201712351

Nickel-Catalyzed Amination of Aryl Fluorides with Primary Amines
Harada, T.; Ueda, Y.; Iwai, T.; Sawamura, M.
Chem. Commun. 2018, 54, 1718–1721.
DOI: 10.1039/C7CC08181B
Synthesis of Cyclobutene-Fused Eight-Membered Carbocycles through Gold-Catalyzed Intramolecular Enyne [2+2] Cycloaddition
Iwai, T.; Ueno, M.; Okochi, H.; Sawamura, M.
Adv. Synth. Catal. 2018, 360, 670–675.
DOI: 10.1002/adsc.201701193
Polystyrene-Cross-Linking Ortho-Substituted Triphenylphosphines: Synthesis, Coordination Properties, and Application to Pd-Catalyzed Cross-Coupling of Aryl Chlorides
Iwai, T.; Asano, K.; Harada, T.; Sawamura, M.
Bull. Chem. Soc. Jpn. 2017, 90, 943–949.
DOI: 10.1246/bcsj.20170141
Asymmetric Synthesis of β-Lactams through Copper-Catalyzed Alkyne–Nitrone Coupling with Prolinol-Phosphine Chiral Ligand.
Takayama, Y.; Ishii, T.; Ohmiya, H.; Iwai, T.; Schwarzer, M. C.; Mori, S.; Taniguchi, T.; Monde, K.; Sawamura, M.
Chem. Eur. J. 2017, 23, 8400–8404.
DOI: 10.1002/chem.201702070
Exploring the Full Catalytic Cycle of Rhodium(I)–BINAP-Catalysed Isomerization of Allylic Amines: A Graph Theory Approach for Path Optimisation.
Yoshimura, T.; Maeda, S.; Taketsugu, T.; Sawamura, M.; Morokuma, K.; Mori, S.
Chem. Sci. 2017, 8, 4475–4488.
DOI: 10.1039/C7SC00401J
Synthesis of α-Quaternary Formimides and Aldehydes through Umpolung Asymmetric Copper Catalysis with Isocyanides.
Hojoh, K.; Ohmiya, H.; Sawamura, M.
J. Am. Chem. Soc. 2017, 139, 2184–2187.
DOI: 10.1021/jacs.6b12881
A Polystyrene-Cross-Linking Bisphosphine: Controlled Metal Monochelation and Ligand-Enabled First-Row Transition Metal Catalysis.
Iwai, T.; Harada, T.; Shimada, H.; Asano, K.; Sawamura, M.
ACS Catal. 2017, 7, 1681–1692.
DOI: 10.1021/acscatal.6b02988
Synthesis, Coordination Properties, and Catalytic Application of Triarylmethane-Monophosphines.
Iwai, T.; Tanaka, R.; Sawamura, M.
Organometallics, 2016, 35, 3959-3969.
DOI: 10.1021/acs.organomet.6b00752

Copper-Catalyzed Enantioselective Allyl–Allyl Coupling between Allylic Boronates and Phosphates with a Phenol/N-Heterocyclic Carbene Chiral Ligand.
Yasuda, Y.; Ohmiya, H.; Sawamura, M.
Angew. Chem. Int. Ed., 2016, 55, 10816-10820.
DOI: 10.1002/anie.201605125
Phosphine-Catalyzed Vicinal Acylcyanation of Alkynoates.                                    
Murayama, H.; Nagao, K.; Ohmiya, H.; Sawamura, M.
Org. Lett., 2016, 181706-1709.
DOI: 10.1021/acs.orglett.6b00677

Copper-Catalyzed Semihydrogenation of Internal Alkynes with Molecular Hydrogen.
Wakamatsu, T.; Nagao, K.; Ohmiya, H.; Sawamura, M.
Organometallics, 2016, 35, 1354-1357.
DOI: 10.1021/acs.organomet.6b00126
Site-selective and Stereoselective C(sp3)–H Borylation of Alkyl Side Chains of 1,3-Azoles with a Silica-Supported Monophosphine-Ir Catalyst.
Murakami, R.; Iwai, T.; Sawamura, M.
Synlett., 2016, 27, 1187-1192.
DOI: 10.1055/s-0035-1561599

Construction of Quaternary Stereogenic Carbon Centers through Copper-Catalyzed Enantioselective Allylic Alkylation of Azoles.
Ohmiya, H.; Zhang, H.; Shibata, S.; Harada, A.; Sawamura, M.
Angew. Chem. Int. Ed., 2016, 55, 4777-4780.

Copper-Catalyzed Stereoselective Conjugate Addition of Alkylboranes to Alkynoates.
Wakamatsu, T.; Nagao, K.; Ohmiya, H.; Sawamura, M.
Beilstein J. Org. Chem., 2015, 11, 2444–2450.
Silica-supported Triptycene-type Phosphine. Synthesis, Characterization, and Application to Pd-Catalyzed Suzuki–Miyaura Cross-coupling of Chloroarenes.
Iwai, T.; Konishi, S.; Miyazaki, T.; Kawamorita, S.; Yokokawa, N.; Ohmiya, H.; Sawamura, M.
ACS Catal., 2015, 5, 7254–7264.
DOI: 10.1021/acscatal.5b00904
Synthesis of 1,1-Diborylalkenes through a Brønsted-base-catalyzed Reaction between Terminal Alkynes and Bis(pinacolato)diboron.
Morinaga, A.; Nagao, K.; Ohmiya, H.; Sawamura, M.
Angew. Chem. Int. Ed., 2015, 54, 15859-15862.
DOI: 10.1002/anie.201509218

Synthesis and Structures of a Chiral Phosphine-Phosphoric Acid Ligand and Its Rhodium(I) Complexes.
Iwai, T.; Akiyama, Y.; Tsunoda, K.; Sawamura, M.
Tetrahedron:Asymmetry, 2015, 26, 1245–1250.
DOI: 10.1016/j.tetasy.2015.09.016

Copper-Catalyzed Enantioselective Allylic Cross-Coupling with Alkylboranes.
Hojoh, K.; Shido, Y.; Nagao, K.; Mori, S.; Ohmiya, H.; Sawamura, M.
Tetrahedron, 2015, 71, 6519–6533.
Copper-Catalyzed g-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes.
Yasuda, Y.; Nagao, K.; Shido, Y.;  Mori, S.; Ohmiya, H.; Sawamura, M.
Chem. Eur. J. 2015, 21, 9666-9670.
 DOI: 10.1002/chem.201501055
Copper(I)-Catalyzed Intramolecular Hydroalkoxylation of Unactivated Alkenes

Murayama, H.; Nagao, K.; Ohmiya, H.; Sawamura, M.
Org. Lett. 2015, 17,  2039–2041.
DOI: 10.1021/acs.orglet.5b00758
Anti-Selective Vicinal Silaboration and Diboration of Alkynoates through Phosphine Organocatalysis.
Nagao, K.; Ohmiya, H.; Sawamura, M.
Org. Lett. 2015, 17, 1304–1307.
DOI: 10.1021/acs.orglett.5b00305

Copper-Catalyzed Enantioselective Allylic Alkylation of Terminal Alkyne Pronucleophiles.
Harada, A.; Makida, Y.; Sato, T.; Ohmiya, H.; Sawamura, M.
J. Am. Chem. Soc. 2014, 136, 13932–13939.
DOI: 10.1021/ja508433